1. Field of the Invention
This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzylic sulfoxides with nonoxidizing acid halides.
2. Description of the Prior Art
Sulfoxides of the general formula RSOR are known to undergo rearrangements under acid conditions to produce alpha-substituted sulfides, the overall result being reduction of the sulfoxide group and oxidation of the adjacent carbon atom. Reactions of this type are generally known as the Pummerer reaction. The products of such Pummerer reactions when acid halides are employed normally include alpha-substituted halomethyl sulfides, or via hydrolysis, the corresponding aldehydes. Russell & Mikol, Mech. Mol. Migr., 1, 157-207 (1968).
Substituted ortho-amino benzyl chloride per se has been described in the prior art but this compound has been produced from the corresponding ortho-amino benzyl alcohol, and not from an amino benzyl sulfoxide.
It is an object of the present invention to provide a process for the conversion of nuclear substituted benzyl sulfoxides to nuclear substituted benzylic halides in good yields.
It is another object of this invention to provide novel ortho-amino benzyl halide compounds which are useful for the preparation of aniline derived herbicide compounds.
It is a further object of this invention to provide a process for making ortho-amino benzyl halide compounds which employs starting materials derived from known aromatic sulfilimine rearrangement products.